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Acta Chimica Sinica >

2012 , Vol. 70 >Issue 10: 1201 - 1206

DOI: https://doi.org/10.6023/A1108182

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Preparation of Axially Chiral Biphenyls by Configuration Transformation Based on Chiral Amino Alcohols

  • Wang Limin ,
  • Cheng Senxiang ,
  • Chen Tong ,
  • Chang Junbiao
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  • a Hi-tech. Research Center, Henan Academy of Sciences, Zhengzhou 450002;
    b Department of Chemistry, Zhengzhou University, Zhengzhou 450001

Received date: 2011-08-18

  Revised date: 2012-01-04

  Online published: 2012-05-16

Supported by

Project supported by the National Outstanding Young Scholar Science Foundation of National Natural Science Foundatiion of China (No. 30825043) and the National Natural Science Foundation of China (No. 20572017).

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Abstract

Axially chiral biphenyls (P, S)-3a and (M, R)-3b were obtained from (M/P)-4,4'-dimethoxy- 5,6,5',6'-bis(methylenedioxy)-2-carboxylester-2'-carboxamide biphenyls via configuration transformation of the biphenyls with (S)-alaninol or (R)-alaninol chiral-arm. Crystal structure of (P, S)-3a was determined. The crystal of (P, S)-3a belongs to monoclinic, space group P2(1), a＝12.122(2) Å, b＝8.9911(18) Å, c＝ 12.779(3) Å, β＝112.38(3)°. There are two kinds of hydrogen-bonding in the (P, S)-3a crystal. The first is hydrogen-bonding between the hydroxyl group of the amino alcohol arm and the amide oxygen of a neighboring molecule. The second is hydrogen-bonding between the amide hydrogen atom and the amide oxygen of a neighboring molecule. Each molecule is linked to its two adjacent molecules by four intermolecular H-bonds. The configuration of (M, R)-3b was assigned based on the CD spectra. In addition, from (P, S)-3a, (P)-2,2'-dihydroxymethyl-4,4'-dimethoxy-5,6,5',6'-bis(methylenedioxy)-biphenyl (6a) was synthesized.

Key words： axially chiral biphenyl; crystallization induced; configuration transformation

Cite this article

Wang Limin , Cheng Senxiang , Chen Tong , Chang Junbiao . Preparation of Axially Chiral Biphenyls by Configuration Transformation Based on Chiral Amino Alcohols[J]. Acta Chimica Sinica, 2012 , 70(10) : 1201 -1206 . DOI: 10.6023/A1108182

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